Subba Reddy, B. V. ; Venkateswarlu, A. ; Borkar, Prashant ; Yadav, J. S. ; Sridhar, B. ; Grée, René (2014) Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in Prins Cyclization: Oxa- versus Thia-Selectivity Journal of Organic Chemistry, 79 (6). pp. 2716-2722. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo402832t
Related URL: http://dx.doi.org/10.1021/jo402832t
Abstract
An unprecedented oxa- versus thia-selectivity has been observed in Prins cyclization of 6-mercaptohex-3-en-1-ol with aldehydes. In the presence of a stoichiometric amount of strong Lewis or Brønsted acids, the reaction provides the hexahydro-2H-thieno[3,2-c]pyran skeleton predominantly via oxonium-Prins cyclization. In contrast, a catalytic amount of weak Lewis or Brønsted acids provides the hexahydro-2H-thiopyrano[4,3-b]furan preferentially through thionium-Prins cyclization.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 135725 |
| Deposited On: | 10 Aug 2023 12:28 |
| Last Modified: | 10 Aug 2023 12:28 |
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